CAS: 84957-29-9; Cefpirome

该化合物是一种被归类为第四代甲状腺素下的广谱状脑膜结膜杆菌抗生素,主要用于治疗各种细菌感染,特别是由包括Pseudomonas aeruginosa在内的克氏阴性细菌引起的感染;Cefpirome对乙状乳腺具有很强的抗抗抗性菌株的抗药性;该化合物的特点是能够抑制细菌细胞壁合成,导致细胞透析和死亡;通常通过静脉注射或肌肉内途径进行,允许快速吸收和在身体中分布;Cefpirome具有相对较低的毒性特征,适合各种病人群体使用,尽管它可能会造成副作用,例如过敏反应或某些人的胃肠紊乱;其致癌性反应涉及肾液排泄,需要对肾功能受损的病人进行剂量调整;

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CAS号63527-52-6 头孢噻肟 | CAS号533-37-9 2,3-环戊烯并吡啶 | CAS号104146-10-3 7-苯乙酰氨基-3-氯甲基-4... | CAS号83421-24-3 7β-[2-(2-aminot... | CAS号86070-92-0 (6R,7R)-7-((Z)-... | CAS号98753-19-6 硫酸头孢匹罗 | CAS号533-37-9 2,3-环戊烯并吡啶 | CAS号104301-63-5 (Z)-2-氨基-alpha-...

合成工艺路线路线简述

  • 533-37-9 + 63527-52-6 = 84957-29-9
    反应条件:1.1 Reagents: Hexamethyldisilazane,Trimethylsilyl Iodide Solvents: Dichloromethane; 7 H,Reflux1.2 Reagents: Trimethylsilyl Iodide Solvents: Dichloromethane; 2 H,Reflux1.3 Reagents: Hydrochloric Acid,Potassium Iodide Solvents: Water; 5 Min,Cooled; 2 H,Cooled; Overnight,4 °C
    标题:Synthesis Of Cefpirome Sulfate Using Dihydrocyclopenta[b]Pyridine And Cefotaxime As Starting Materials
    作者:Tang,Lei; Wang,Jian-Ta; Zhu,Gao-Feng
    参考文献:Huaxue Shiji 日期:2008 卷标:30(4) 页码:304-305]

    533-37-9 + 60846-21-1 = 84957-29-9 [标题:Reaction Conditions
    标题:Cephem Compounds
    参考文献:Federal Republic Of Germany]

    496-15-1 + 63527-52-6 = 84957-29-9
    反应条件:1.1 Reagents: N,O-Bis(Trimethylsilyl)Acetamide Solvents: Acetonitrile1.2 Reagents: Trimethylsilyl Iodide1.3 Solvents: Acetonitrile,Tetrahydrofuran1.4 Reagents: N,O-Bis(Trimethylsilyl)Acetamide Solvents: Acetonitrile
    标题:Synthesis Of Cephalosporin Derivatives With Different 3'-Nitrogen Heterocyclic Substituents
    作者:Petek,Alenka Stefanic; Japelj,Miha
    参考文献:Acta Pharmaceutica (Zagreb) 日期:2000 卷标:50(1) 页码:17-27]

    533-37-9 + 66340-28-1 = 84957-29-9 [标题:Reaction Conditions
    标题:Preparation Of Cephalosporin Derivatives As Intermediates For Antibiotics
    参考文献:European Patent Organization]

    533-37-9 + 82423-07-2 + 178036-40-3 = 84957-29-9 [标题:Reaction Conditions
    标题:Cephem Compounds
    参考文献:Federal Republic Of Germany
(6R,7R)-3-((6,7-Dihydro-5H-Cyclopenta[b]Pyridin-1-Ium-1-yl)Methyl)-8-Oxo-7-(2-Phenylacetamido)-5-Thia-1-Azabicyclo[4.2.0]oct-2-Ene-2-Carboxylate置于青霉素(酰胺)酶体系中,用 四氢呋喃,水 作为反应溶剂,化学反应 6.5H,反应生成 头孢匹罗
参考文献:One-Pot Synthesis Of Cefpirome Sulfate From Gcle
标题:One-Pot Synthesis Of Cefpirome Sulfate From Gcle
摘要:[image Omitted] Cefpirome Was Synthesized In 37.7% Overall Yield From 3-Chloromethyl-7-Phenylacetylamino Cephalosporanic Acid P-Methoxybenzyl Ester (Gcle) By Sequential Substitution Of C-3 Chloride With Iodide And 2,3-Cyclopentenopyridine,Followed By A One-Pot Procedure Including Deprotection Of Carboxyl Group,Hydrolysis Of 7-Phenylacetamido,And Reaction With 2-Mercaptobenzothiazolyl-(Z)-2-(2-Aminothiazol-4-yl)-2-Methoxyiminoacetate (Maem). The Reaction Conditions Were As Follows: Obtained From Gcle At Low Temperature (-5 To 0 Degrees C) And Absence Of Light,3-Iodomethyl-7-Phenylacetylamino Cephalosporanic Acid P-Methoxybenzyl Ester (Gile) Without Purification Was Reacted Directly With 2,3-Cyclopentenopyridine,In Which The Molar Ratio Of Gcle,Nai,And 2,3-Cyclopentenopyridine Was 1:2:4,And The Molar Ratio Of The Resulting Compound P-Methoxybenzyl 7-Phenylacetylamido-3-(2,3-Cyclopenteno-1-Pyridinio)Methyl-3-Cephem-4-Carboxylate Iodide And Maem Was 1:1.1. The Structure Of The Intermediate And The Target Compound Obtained Were Determined By Nuclear Magnetic Resonance Spectra And Mass Spectroscopy.
DOI:10.1080/00397911003629499

海关参考信息

专利信息


专利号:US-8017776-B2
优先权日:2003-07-15
标题 :Methods for synthesis of acyloxyalkyl compounds
发明人:BHAT LAXMINARAYAN; GALLOP MARK A
权利人:XENOPORT INC
摘要:Disclosed herein are methods for synthesizing 1-(acyloxy)-alkyl prodrug derivatives of drugs through oxidation of 1-acyl-alkyl derivatives of drugs under anhydrous reaction conditions. The methods typically proceed stereospecifically, in high yield, do not require the use of activated intermediates and/or toxic compounds and are readily amenable to scale-up.

专利号:WO-2012095438-A1
优先权日:2011-01-12
标 题 :Particles and suspensions of cephalosporin antibiotics
发明人:NIEDERMANN HANS PETER; BOTHE HEIKO
权利人:INTERVET INT BV; NIEDERMANN HANS PETER; BOTHE HEIKO
摘要:Disclosed is a method of making particles of a cephalosporin antibiotic, particularly cefquinome, wherein use is made of diafiltration. The diafiltration can be with anti- solvent, in which case a precipitate is obtained of particles as such. The diafiltration can also be with a pharmaceutically acceptable suspension medium. In that case several process steps of isolating, drying, transporting of particles can be avoided, because the suspension resulting from the synthesis of the particles is directly turned into a final drug product formulation.

专利号:US-9066864-B2
优先权日:2011-01-12
标 题:Use of liquid medium exchange by cross flow filtration in the preparation of drug suspensions
发明人:NIEDERMANN HANS PETER; BOTHE HEIKO
权利人:NIEDERMANN HANS PETER; BOTHE HEIKO; INTERVET INC
摘要:Disclosed is a method of making particles of a drug wherein use is made of diafiltration. The diafiltration can be with anti-solvent, in which case a precipitate is obtained of particles as such. The diafiltration can also be with a pharmaceutically acceptable suspension medium. In that case several process steps of isolating, drying, transporting of particles can be avoided, because the suspension resulting from the synthesis of the particles is directly turned into a final drug product formulation.

专利号:US-8143437-B2
优先权日:2002-02-19
标题:Methods for synthesis of prodrugs from 1-acyl-alkyl derivatives and compositions thereof
发明人:GALLOP MARK A; XIANG JIA-NING; YAO FENMEI; BHAT LAXMINARAYAN; ZHOU CINDY X
权利人:GALLOP MARK A; XIANG JIA-NING; YAO FENMEI; BHAT LAXMINARAYAN; ZHOU CINDY X; XENOPORT INC
摘要:The present invention provides a method for synthesizing 1-(acyloxy)-alkyl derivatives from 1-acyl-alkyl derivatives, which typically proceeds stereospecifically, in high yield, does not require the use of activated intermediates and/or toxic compounds and is readily amendable to scale-up. The current invention also provides 1-acyl-alkyl derivatives of known drug components and methods for synthesizing these 1-acyl-alkyl derivatives.

专利号:US-7452990-B2
优先权日:2002-12-26
标题 :Intermediates for synthesis of cephalosporins and process for preparation of such intermediates
发明人:DATTA DEBASHISH; DANTU MURALIKRISHNA; MISHRA BRIJKISHORE; SHARMA POLLEPEDDI LAKSHMI NARAYANA
权利人:LUPIN LTD
摘要:A novel 4-halo-2-oxyimino-3-oxo butyric acid-N,N-dimethyl formiminium chloride chlorosulfate of formula (I) useful in the preparation of cephalosporin antibiotics n nwhereinn n X is chlorine or bromine; R is hydrogen, C 1-4 alkyl group, an easily removable hydroxyl protective group, —CH 2 COOR 5 , or —C(CH 3 ) 2 COOR 5 , wherein R 5 is hydrogen or an easily hydrolysable ester group. The compound of formula (I) is prepared by reacting 4-halo-2-oxyimino-3-oxobutyric acid of formula (IV 1 ), n nwherein X, R and R 5 are as defined above, with N,N-dimethylformiminium chloride chlorosulphate of formula (VII)n n nin an organic solvent at a temperature ranging from −30° C. to −15° C. The cephalosporins that may be prepared from the intermediate include cefdinir, cefditoren pivoxil, cefepime, cefetamet pivoxil, cefixime, cefmenoxime, cefodizime, cefoselis, cefotaxime, cefpirome, cefpodoxime proxetil, cefquinome, ceftazidime, cefteram pivoxil, ceftiofur, ceftizoxime, ceftriaxone and cefuzonam.

专利号:US-9006421-B2
优先权日:2013-03-14
标题 :Cephalosporin compositions and methods of manufacture
发明人:LAI JAN-JI; PATHARE PRADIP M; KOLLA LAXMA; SORET ADRIEN F
权利人:CUBIST PHARM INC
摘要:Provided herein is a method for the synthesis of cephalosporin antibiotic compounds comprising the conversion of a protected 7-amino group into a 7-carboxamide moiety in a single step.
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主要参考文献


1: Deshayes S, Coquerel A, Verdon R. Neurological Adverse Effects Attributable to β-Lactam Antibiotics: A Literature Review. Drug Saf. 2017 Dec;40(12):1171-1198. doi: 10.1007/s40264-017-0578-2. Review. Review. Spanish. doi: 10.1186/cc10441. Epub 2011 Sep 13. Review.
4: Livermore DM, Hope R, Mushtaq S, Warner M. Orthodox and unorthodox clavulanate combinations against extended-spectrum beta-lactamase producers. Clin Microbiol Infect. 2008 Jan;14 Suppl
1:189-93. Review. Erratum in: Clin Microbiol Infect. 2008 May;14 Suppl

合成参考文献


参考文献:10.1128/aac.40.9.1973
摘要:Bajaksouzian S, Visalli MA, Jacobs MR, Appelbaum PC. Antipneumococcal activities of cefpirome and cefotaxime, alone and in combination with vancomycin and teicoplanin, determined by checkerboard and time-kill methods. Antimicrob Agents Chemother. 1996 Sep;40(9):1973–6.
参考文献:10.1007/s001340050885
摘要:Jacolot A, Incagnoli P, Edouard AR, Tod M, Petitjean O, Samii K, Mimoz O. Pharmacokinetics of cefpirome during the posttraumatic systemic inflammatory response syndrome. Intensive Care Med. 1999 May;25(5):486–91. doi: 10.1007/s001340050885.
参考文献:10.2302/kjm.48.93
摘要:Kaburaki J, Yamada M, Kamikawara M, Konosu Y, Iwase M, Uehara S, Kikuchi H. In vivo and in vitro positive interference by cefpirome in measurement of serum creatinine by the Jaffe method. Keio J Med. 1999 Jun;48(2):93–6. doi: 10.2302/kjm.48.93.
参考文献:10.1016/j.ijantimicag.2003.08.009
摘要:Bergeret M, Boutros N, Raymond J. In vitro combined bactericidal activity of cefpirome and glycopeptides against glycopeptides and oxacillin-resistant staphylococci. International Journal of Antimicrobial Agents. 2004 Mar;23(3):247–53. doi: 10.1016/j.ijantimicag.2003.08.009.
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